You know something needs to be said.
Maybe there is a problem in your marriage, something happening at work, a disagreement with a family member, or a situation with a friend that has gone on too long. You have thought about bringing it up, perhaps more than once.
But then the questions start.
What if they get angry? What if I hurt them? What if I say it wrong? What if I embarrass myself or sound stupid? What if I get flustered and can’t explain what I mean? What if I make everything worse?
So you wait.
Sometimes waiting is wise. We don’t need to address every irritation the moment we experience it, and there are times when we genuinely aren’t prepared to have a productive conversation.
But sometimes waiting becomes avoiding.
The problem remains while we continue hoping there might eventually be an easier way to address it.
So how do you have a difficult conversation without making things worse?
The first thing to recognize is something we may not want to hear:
You can’t guarantee that you won’t.
You can control what you say, how you prepare, and how you conduct yourself. You cannot control how another person will respond.
The objective isn’t to eliminate every possible negative outcome before speaking. It is to determine whether something needs to be said, learn how to say it wisely, prepare for what you reasonably can, and then handle your part of the conversation well.
Does This Actually Need to Be Said?
Before asking how to have a difficult conversation, there is another question worth asking:
Does this conversation need to happen?
Not everything that bothers us needs to be confronted.
Sometimes we are irritated. Sometimes we misunderstand what happened. Sometimes we make assumptions about another person’s motives. Sometimes what seems enormously important today won’t matter much tomorrow.
So before deciding what to say, examine what happened.
What do you actually know? What are you assuming? Is something genuinely wrong? Does something need to be corrected, clarified, resolved, or simply understood?
And perhaps most importantly:
Is what you intend to say true?
Feeling strongly about something doesn’t make our interpretation of it correct.
At the same time, the fact that addressing something will be uncomfortable doesn’t mean it should be ignored.
A useful principle is:
Don’t have a difficult conversation merely because you’re upset. But don’t avoid a necessary conversation merely because it’s uncomfortable.
Talk About the Problem Without Condemning the Person
Once you’ve determined that something needs to be addressed, identify exactly what the problem is.
There is an important difference between:
“You didn’t follow through on what you said you would do.”
and:
“You’re completely unreliable.”
The first addresses something the person did. The second makes a judgment about who the person is.
There is also a difference between:
“You made that decision before you had all the information.”
and:
“You never think anything through.”
Anger can make exaggeration feel justified. Words such as always and never can make our argument sound stronger while actually making it less truthful.
Once legitimate criticism gets mixed with exaggeration or condemnation, we also give the other person something false to defend against. They may become so focused on what isn’t true that they never hear the part that is.
This works from the other direction as well. Learning to separate what is true from exaggeration or condemnation can also help us respond more wisely when we are the one receiving criticism.
If something needs addressing, identify it as accurately as possible.
Truth doesn’t need exaggeration or condemnation to make it stronger.
Knowing What to Say Isn’t the Same as Knowing How to Say It
Sometimes we aren’t avoiding a difficult conversation because we’re unwilling to address the problem.
We genuinely don’t know how.
How do I say this without hurting them?
How do I explain what happened without sounding accusatory?
How do I tell them what I believe is true without starting an argument?
Those are legitimate concerns.
The answer isn’t simply, “Just say what needs to be said.”
Presentation matters. Timing matters. Tone matters. Words matter.
And something else matters that is often overlooked:
The person you’re talking to matters.
We naturally tend to communicate in ways that make sense to us. The problem is that the person sitting across from us may not naturally process information the way we do.
Know Yourself—and Know the Person You’re Talking To
Some people naturally want you to get to the point. Tell them what happened, what the problem is, and what needs to be done.
Another person may be listening first for what the conversation means for the relationship. A blunt presentation that one person considers efficient may sound unnecessarily harsh to them.
Someone else may want facts, examples, and enough information to understand how you reached your conclusion.
Another may respond better when the issue is presented clearly, specifically, and in an orderly way rather than introduced unexpectedly and allowed to move in several directions at once.
None of those approaches changes what is true.
They change how truth is communicated.
This is why knowing yourself and understanding others can make such a difference in communication.
Ask yourself how you are naturally inclined to communicate. Are you likely to be so direct that you overlook how your words affect the other person? Are you likely to soften the message so much that the real issue disappears? Are you going to provide far more information than the conversation requires? Are you so concerned with keeping the conversation orderly that you leave little room for the other person to respond?
Then consider the person you’re speaking to.
What helps them understand? How are they likely to hear what you’re about to say?
Good communication isn’t merely saying something the way I would want to hear it. It involves learning enough about another person to communicate in a way that gives them a reasonable opportunity to understand what I actually mean.
Without that knowledge, even a thoughtful presentation contains some guesswork.
But we can learn more about ourselves and others.
The free STAR Personality Course is one way to better understand how you naturally approach communication and how other people may process the same conversation differently.
The truth doesn’t have to change because the listener is different. The way we communicate it should.
What Are You Afraid Will Happen?
Even after deciding what needs to be said and thinking carefully about how to say it, we may still hesitate.
This is where another question becomes useful:
What am I actually afraid of?
Don’t settle for, “I hate confrontation.”
Be more specific.
I’m afraid they’ll get angry.
I’m afraid I’ll hurt them.
I’m afraid they’ll reject me.
I’m afraid I’ll embarrass myself.
I’m afraid I’ll sound stupid.
I’m afraid I’ll get flustered and forget what I wanted to say.
I’m afraid they’ll turn everything around on me.
I’m afraid I’ll make the situation worse.
Naming the fear allows us to examine it.
“They’re going to get angry” may be possible, but unless you know the future, it is a prediction rather than a fact.
“I’ll embarrass myself” is also a prediction.
“I may get flustered” could be a realistic possibility. But getting flustered doesn’t necessarily mean the conversation shouldn’t happen.
Some fears identify something useful. If you’re concerned you’ll forget what you want to say, make notes. If you’re afraid anger will take over, don’t begin the conversation while you’re angry. If you’re concerned your words will sound like a personal attack, think through how you can address the problem rather than condemn the person. If you’re afraid of being misunderstood, consider how the other person tends to receive information.
Fear can provide information worth examining without being given authority to make the decision.
When Preparation Becomes Avoidance
Preparation is not the enemy.
Sometimes “I’m not ready to have this conversation” is completely true.
We may need more information. We may need to calm down. We may need to decide what we actually want to accomplish. We may need to learn a better way to communicate what needs to be said.
But preparation has a stopping point.
Eventually we may know what needs addressing, know reasonably well how we want to address it, and still feel uncomfortable.
That’s when we need to distinguish between:
I’m not prepared yet.
and:
I’m waiting until I’m no longer uncomfortable.
There is no amount of preparation that can guarantee how another person will respond.
And avoiding the conversation offers something that preparation cannot:
Immediate relief.
We don’t have to experience the embarrassment, tension, uncertainty, rejection, anger, or whatever else we’re afraid might happen.
For the moment, we feel better.
But the problem that made the conversation necessary may still be there.
Discomfort tells us something is difficult. It does not automatically tell us what we should do.
The desire to escape discomfort can be very real without being allowed to make the decision for us.
A Difficult Conversation I Had at 25
When I was 25 years old, I faced a difficult conversation that I still remember more than 40 years later.
In 1985, I worked as a press operator for a small family-owned printing company in Worcester, Massachusetts. The owners were good people and, when things went well, it was a good job. But organization wasn’t one of the company’s strengths.
Finding the right die for a printing job could take 45 minutes or more. Ink needed for a job might or might not be available. Paper wasn’t organized in a way that made shortages obvious. Sometimes a press would be completely set up before discovering that the die needed for the job was damaged and had to be sent out for repair.
I began making some changes.
I found the maintenance manual for my press, read it, and started following a regular maintenance schedule. Many of the breakdowns I had previously experienced disappeared.
While my press was running, I organized the ink room and established a simple inventory system that the other press operators agreed to follow. I organized and labeled the dies so they could be located more easily and protected when they were returned to storage. I organized the paper by size and finish so shortages could be seen.
Eventually, I reorganized the finished-label inventory as well. Before the change, monthly inventory required about seven people working roughly five hours, and the count still didn’t always come out right. Afterward, it took three people about four hours to finish.
I had done all of this without interfering with my regular responsibility of running my press.
Then the company announced that annual raise reviews were coming.
At the time, I was making $7 an hour. At this company, a 25-cent hourly raise was considered a pretty good raise.
I started wondering what the improvements I had made were actually worth.
So I sat down and evaluated them. I prepared charts showing the time that had been spent looking for things before the changes and what was happening afterward. I documented the improvements and the labor they were saving. I also documented that my own production had increased, despite the time I had spent away from my press making these improvements.
When I finished looking at everything, I reached a conclusion:
I was going to ask for a $2-an-hour raise—from $7 to $9 an hour.
I was scared to death.
I hadn’t discussed the idea with anyone at the shop—not even my shop supervisor. I didn’t know exactly what I was going to say, how I was going to say it, or how the owners would respond.
Would they think the request was ridiculous?
Would they laugh?
Would I embarrass myself?
Would they simply say no?
Several times I talked myself out of asking.
After all, my job was already easier and more pleasant because of the improvements I had made. Maybe that should be enough reward.
And if I decided not to ask, one thing would happen immediately:
I wouldn’t have to face the conversation.
The anxiety would subside. I wouldn’t risk hearing no. I wouldn’t risk embarrassment.
But another thought kept nagging at me. The changes hadn’t just improved my working conditions. They had made things easier for other employees and saved the company time and money.
I believed that had value and that it was reasonable to ask to be compensated for it.
So I prepared the best way I knew how.
I need to make something clear here: I didn’t know the process I’m describing in this article when I was 25.
I wasn’t consciously working through principles about truth, fear, comfort, personality, or communication. I didn’t have a framework for difficult conversations.
I was simply using my own best thinking to figure out how to handle something that frightened me.
Looking back today, however, I can see many of the same elements we’ve been discussing.
The day of the reviews arrived, and I was still scared.
One employee after another went into the office and returned quietly to work. There was an unwritten rule among the shop workers: you didn’t tell your coworkers what you made or what kind of raise you had received.
Eventually it was my turn.
I sat down with one of the owner’s sons, laid out my charts and documentation, and explained what I had done as best I could.
Then I told him:
“I want a $2-an-hour raise.”
He quietly gathered my paperwork, got up, and went into another office where he talked with his father, brother, and sister.
I waited.
There was nothing more I could do.
I had prepared my case. I had presented it. I had made the request.
Their response belonged to them.
Eventually he returned, shook my hand and said, “Congratulations. You have your $2-an-hour raise.”
They gave me the entire amount and thanked me for what I had done.
My hourly pay went from $7 to $9. It remains the largest hourly raise I’ve ever received.
I didn’t walk back into the shop and announce what had happened. I followed the same unwritten rule everyone else did and simply went back to work. My shop supervisor apparently learned about it through the owners and later congratulated me privately.
But the most important part of this story isn’t that they gave me the raise.
I didn’t know they were going to say yes when I decided to ask.
They could have declined. They could have offered less. They could have thought the request was unreasonable.
The favorable outcome doesn’t prove that having the conversation was the right decision any more than an unfavorable outcome would have proved it was the wrong one.
Before I knew the outcome, I had to decide whether I had a legitimate basis for the request, gather the facts, figure out the best way I knew to present them, prepare for what I reasonably could—and then decide whether my fear was going to prevent me from having the conversation.
I didn’t become comfortable first.
I was afraid when I walked into the office.
The fear didn’t have to disappear for me to act.
What That Story Can Teach Us
The circumstances of your difficult conversation will probably be very different from mine.
It may involve your spouse, a parent, an adult child, a friend, an employer, an employee, or someone else entirely.
But the questions remain remarkably similar.
Does this need to be said?
Determine what is actually true. Don’t confuse irritation, assumption, or emotion with fact.
How should I say it?
Address the issue without condemning the person. Consider how you naturally communicate and how the other person is likely to understand what you’re saying.
What am I afraid will happen?
Name the fear. Examine it. If it identifies something you can reasonably prepare for, prepare.
Am I waiting because I’m unprepared—or because I want the discomfort to go away?
There comes a point when more preparation cannot eliminate uncertainty.
Am I willing to do what I’ve determined needs to be done even though I’m still uncomfortable?
Knowing a better way and actually practicing it are two different things. Changing familiar responses requires us to practice something different.
That’s where knowledge has to become action.
You Are Responsible for Your Part
One of the reasons difficult conversations are difficult is that we want assurance about the outcome.
If I say this correctly, will they understand?
Will they agree?
Will they stay calm?
Will they forgive me?
Will they change?
We don’t get to know those answers beforehand.
You can be calm and the other person can become angry. You can be truthful and they can disagree. You can be considerate and they can still feel hurt. You can explain yourself clearly and they can still misunderstand you.
That doesn’t make preparation or good communication unimportant.
It establishes the limits of our responsibility.
You are responsible for your part of the conversation. The other person is responsible for theirs.
Waiting until you can control both sides means you may wait forever.
A Better Way to Approach Difficult Conversations
So how do you have a difficult conversation without making things worse?
You can’t guarantee that you won’t make things worse.
But you can greatly reduce unnecessary harm.
Determine whether something actually needs to be said. Make sure what you intend to address is true. Separate the problem from your judgment of the person. Consider how you naturally communicate and how the other person understands communication. Identify what you’re afraid will happen. Prepare for what you reasonably can.
Then recognize when preparation has become waiting for a guarantee you cannot have.
The principles to practice are straightforward:
Determine what is true before deciding what needs to be said.
Address the problem without condemning the person.
Know yourself and consider the person you’re speaking to.
Examine fear instead of automatically obeying it.
Prepare for what you reasonably can without waiting for certainty.
Don’t let discomfort alone determine what you do.
Do your part well and allow the other person to be responsible for their response.
The goal of a difficult conversation isn’t to guarantee a comfortable outcome.
It is to handle what needs to be said truthfully, wisely, and with consideration for the person hearing it—and then have the courage to say it.
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